(This is putting aside, of course, the fact that we still don't know the whole story of the Dharma Initiative, why they couldn't get along with The Hostiles, how/why the purge occurred, or Ben's complete role in that event. What we do know is that Emerson played Ben throughout season three of Lost as a hyper-civilized sociopath — an interpretation that reached its pinnacle in "The Man Behind the Curtain" episode's flashback to the purge.)
So allow me to speculate that perhaps Michael Emerson's unease with Kaspar Gutman is one of those factors that he draws on (consciously or unconsciously) to make us uneasy with Ben Linus. After all, an actor can find inspiration in the strangest places. It's well known that Anthony Hopkins' characterization of Hannibal Lecter was inspired in part by HAL in 2001: A Space Odyssey!
Speaking of which, let me add that the "off-the-grid" choice of Sidney Greenstreet tells you everything you need to know about why Michael Emerson is qualified to play creepy... and why I'm not. I would have gone for a perfectly obvious creepy performance and probably selected Hannibal Lecter for this slot. Emerson's choice, on the other hand, is so unexpected that it's inspired.
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